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619-66-9 Usage

Application

4-Formylbenzoic acid is also called 4-Carboxybenzaldehyde. Its molecular formula is C8H5O3, it is insoluble in water, it can be dissolved in DMF, it can undergo esterification reaction and alcohol-aldehyde condensation reaction with alcohol. An important intermediate for organic synthesis, widely used in medicine, pesticides, coatings, liquid crystal raw materials, polymer materials and perfume raw materials.

Uses

Different sources of media describe the Uses of 619-66-9 differently. You can refer to the following data:
1. A metabolite of aldehydes.
2. 4-Formylbenzoic acid is usually used as reagent during esterification of 2,2,6,6-tetramethyl-4-oxopiperidinyl-1-oxyl to yield 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 4-formylbenzoate.
3. 4-Carboxybenzaldehyde is an important intermediate in the synthesis of terepthalic acid. It has been used as reagent during esterification of 2,2,6,6-tetramethyl-4-oxopiperidinyl-1-oxyl to yield 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 4-formylbenzoate.

General Description

4-Formylbenzoic acid is an important intermediate in the synthesis of terepthalic acid. It reacts with barium carbonate to yield two-dimensional barium(II) coordination polymer.

Check Digit Verification of cas no

The CAS Registry Mumber 619-66-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 619-66:
(5*6)+(4*1)+(3*9)+(2*6)+(1*6)=79
79 % 10 = 9
So 619-66-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H,(H,10,11)/p-1

619-66-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A15277)  4-Carboxybenzaldehyde, 98%   

  • 619-66-9

  • 10g

  • 573.0CNY

  • Detail
  • Alfa Aesar

  • (A15277)  4-Carboxybenzaldehyde, 98%   

  • 619-66-9

  • 50g

  • 1557.0CNY

  • Detail
  • Alfa Aesar

  • (A15277)  4-Carboxybenzaldehyde, 98%   

  • 619-66-9

  • 250g

  • 6670.0CNY

  • Detail

619-66-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Formylbenzoic acid

1.2 Other means of identification

Product number -
Other names 4-Formyl-benzoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:619-66-9 SDS

619-66-9Synthetic route

terephthalaldehyde,
623-27-8

terephthalaldehyde,

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With carbon dioxide; potassium carbonate; 1,3-bis(mesityl)imidazolium chloride In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 72h;95%
4-formyl-N,N-bis(pyridin-2-ylmethyl)benzamide
1314659-42-1

4-formyl-N,N-bis(pyridin-2-ylmethyl)benzamide

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
Stage #1: 4-formyl-N,N-bis(pyridin-2-ylmethyl)benzamide With methanol; copper(II) bis(trifluoromethanesulfonate) at 20℃; for 16h;
Stage #2: With barium(II) hydroxide In methanol; water at 20℃;
Stage #3: With hydrogenchloride In methanol; water
99%
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With air; hydrogen bromide; acetic acid; cobalt(II) acetate; manganese(II) acetate at 180℃; under 25745 Torr; for 0.166667h;A 98.3%
B 1.4%
With 9,10-Dibromoanthracene; acetic acid; cobalt(II) acetate; cerium(III) acetate at 165℃; under 25745 Torr; for 0.166667h;A 98.2%
B 1.1%
With 9,10-Dibromoanthracene; acetic acid; cobalt(II) acetate; manganese(II) acetate at 170℃; under 25745 Torr; for 0.166667h;A 97.5%
B 1.9%
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

C

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

D

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With hydrogen bromide; oxygen; acetic acid; cobalt(II) acetate; manganese(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;A 98.1%
B 0.2%
C 0.4%
D 0.4%
With oxygen; acetic acid; palladium diacetate; antimony(III) acetate In water at 182 - 195℃; under 16501.7 - 20929.4 Torr; for 1 - 1.5h; Product distribution / selectivity;A 50.3%
B 7.2%
C 6.4%
D 6.2%
With hydrogen bromide; oxygen; acetic acid; zirconium oxyacetate; cobalt(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;A 4.9%
B 3%
C 1.9%
D 36.9%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;98%
carbon dioxide
124-38-9

carbon dioxide

5,5-dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane
128376-65-8

5,5-dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;97%
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In tetrahydrofuran at 70℃; under 15201 Torr; for 16h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;
76%
potassium formate
590-29-4

potassium formate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With [PhCOPd(PtBu3)I]; dtbpf In diethylene glycol dimethyl ether at 120℃; for 18h; Inert atmosphere;97%
diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With potassium trimethylsilonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h;97%
carbon dioxide
124-38-9

carbon dioxide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: 4-bromo-benzaldehyde With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 2h; Schlenk technique; Sealed tube;
97%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique;
Stage #2: 4-bromo-benzaldehyde With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 6h; Schlenk technique;
66%
acetic acid
64-19-7

acetic acid

p-Toluic acid
99-94-5

p-Toluic acid

A

terephthalic acid
100-21-0

terephthalic acid

B

3-hydroxymethyl-benzoic acid
3006-96-0

3-hydroxymethyl-benzoic acid

C

p-acetoxymethyl benzoic acid
15561-46-3

p-acetoxymethyl benzoic acid

D

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate at 150℃; under 22800 Torr; for 3h;A 95%
B n/a
C n/a
D n/a
3-hydroxymethyl-benzoic acid
3006-96-0

3-hydroxymethyl-benzoic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With LACTIC ACID; dihydrogen peroxide at 30℃; for 7h;95%
With Burgess Reagent; dimethyl sulfoxide at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;92%
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water for 24h; Reflux; Green chemistry;90%
carbon dioxide
124-38-9

carbon dioxide

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: 4-chlorobenzaldehyde With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 5h; Schlenk technique; Sealed tube;
93%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique;
Stage #2: 4-chlorobenzaldehyde With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 16h; Schlenk technique;
41%
methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With water; potassium hydroxide In methanol at 20℃; for 18h;92%
Stage #1: methyl 4-formylbenzoate With water; sodium hydroxide In methanol
Stage #2: In water Acidic conditions;
80%
With sulfuric acid
With lithium hydroxide In tetrahydrofuran; methanol
With water; sodium hydroxide In methanol at 20℃; for 4h;
p-Trimethylsiloxymethylbenzoesaeure
34301-39-8

p-Trimethylsiloxymethylbenzoesaeure

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.916667h; Heating;90%
4-<(tetrahydropyran-2-yloxy)methyl>benzoic acid
104292-82-2

4-<(tetrahydropyran-2-yloxy)methyl>benzoic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.833333h; Heating;90%
4-formylphenyl 2,3,4,5,6-pentafluorobenzenesulfonate

4-formylphenyl 2,3,4,5,6-pentafluorobenzenesulfonate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;90%
benzyl 4-formylbenzoate
78767-55-2

benzyl 4-formylbenzoate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere;90%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;90%
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

C

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With carbon dioxide; oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate In acetic acid at 60℃; under 44269 Torr; for 1h; Product distribution / selectivity;A 89.2%
B n/a
C n/a
With oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate In acetic acid at 25 - 125℃; under 12049.9 - 44475.9 Torr; for 1 - 6h; Product distribution / selectivity;A 79.77%
B 0.67%
C 0.3%
With carbon dioxide; oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt acetylacetonate In acetic acid at 60℃; under 49337.2 Torr; for 1h; Product distribution / selectivity;A 74%
B n/a
C n/a
C12H12O6

C12H12O6

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With poly(amidoamine) dendrimer functionalized sulfonic acid In methanol at 20℃; for 0.25h;89%
4-(Methoxymethyl)benzoic acid
67003-50-3

4-(Methoxymethyl)benzoic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With nitric acid In dichloromethane at 20℃; for 1h;88%
C16H20O2

C16H20O2

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With diethoxymethylane; ferric benzoylacetonate In i-Amyl alcohol at 100℃; for 24h;85%
terephthalic acid
100-21-0

terephthalic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With 1,2-bis(2,4,8,10-tetra-tert-butyl-5,7-dioxa-6-phosphadibenzo[a,c]cyclohepten-6-yloxy)ethane; methylphenylsilane; copper(l) cyanide; 2,2-dimethylpropanoic anhydride In dimethyl sulfoxide at 80℃; for 20h; Schlenk technique; Inert atmosphere;84%
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

3-hydroxymethyl-benzoic acid
3006-96-0

3-hydroxymethyl-benzoic acid

C

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

D

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; manganese(II) acetate; cobalt(II) acetate In acetic acid at 100℃; under 760 Torr; for 14h; Kinetics; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; Temperatures; ratio;A 82%
B n/a
C n/a
D 4%
4-(trifluormethanesulfonyloxy)benzaldehyde
17763-69-8

4-(trifluormethanesulfonyloxy)benzaldehyde

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;81%
4-(hydroxylmethyl)benzaldehyde
52010-97-6

4-(hydroxylmethyl)benzaldehyde

A

terephthalic acid
100-21-0

terephthalic acid

B

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique;A 6 %Spectr.
B 80%
Multi-step reaction with 2 steps
1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 24 h / 25 °C / pH 8 / Enzymatic reaction
2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 7 / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction
2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 7 / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction
2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 7 / Enzymatic reaction
View Scheme
formic acid
64-18-6

formic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;77%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;75%
H2O*CHLiO2

H2O*CHLiO2

p-(iodophenyl)carboxaldehyde
15164-44-0

p-(iodophenyl)carboxaldehyde

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With formic acid; 1,3-bis-(diphenylphosphino)propane; nickel(II) acetate tetrahydrate; acetic anhydride In tetrahydrofuran at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;76%
4-mercaptomethylbenzoic acid
39088-65-8

4-mercaptomethylbenzoic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation;74%
p-aminomethylbenzoic acid
56-91-7

p-aminomethylbenzoic acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With copper(I) 2-hydroxy-3-methylbenzoate; oxygen; ascorbic acid In N,N-dimethyl acetamide at 40℃; for 2h; chemoselective reaction;67%
With riboflavin tetraacetate In dimethylsulfoxide-d6; water-d2 for 0.166667h; Irradiation; In air;
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-formylbenzoyl chloride
16173-52-7

4-formylbenzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃;100%
With oxalyl dichloride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 2h;100%
With thionyl chloride In toluene for 1.5h; Heating;97.9%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

ethylenediamine
107-15-3

ethylenediamine

C18H16N2O4
178241-13-9

C18H16N2O4

Conditions
ConditionsYield
In 1,4-dioxane; ethanol100%
benzyl bromide
100-39-0

benzyl bromide

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

benzyl 4-formylbenzoate
78767-55-2

benzyl 4-formylbenzoate

Conditions
ConditionsYield
Stage #1: 4-Carboxybenzaldehyde With alkali metal carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;
100%
With caesium carbonate In ethyl acetate; N,N-dimethyl-formamide97%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;97%
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

N-butylamine
109-73-9

N-butylamine

N-butyl-4-(1-hydroxy-but-3-enyl)-benzamide

N-butyl-4-(1-hydroxy-but-3-enyl)-benzamide

Conditions
ConditionsYield
Multistep reaction;100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-formylphenyl isocyanate
111616-43-4

4-formylphenyl isocyanate

Conditions
ConditionsYield
With diphenylphosphoranyl azide; triethylamine In dichloromethane for 6h; Heating;100%
With diphenyl phosphoryl azide; triethylamine In dichloromethane for 6h; Reflux;100%
Multi-step reaction with 3 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 °C
2: sodium azide / water; acetone / 1 h / 0 °C
3: toluene / 1 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / tetrahydrofuran / 2 h / Inert atmosphere
2: sodium azide / water / 1 h
3: toluene / 2 h / Inert atmosphere; Reflux
View Scheme
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

allylgallium dichloride
424819-51-2

allylgallium dichloride

4-(1-hydroxybut-3-en-1-yl)benzoic acid

4-(1-hydroxybut-3-en-1-yl)benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran; hexane at 0℃; for 0.8h;100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

poly(ethylene glycol), MW = 4000

poly(ethylene glycol), MW = 4000

poly(ethylene glycol), ester with 4-formylbenzoic acid

poly(ethylene glycol), ester with 4-formylbenzoic acid

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

ethyl N-(2-carboxyphenoxy)acetimidate

ethyl N-(2-carboxyphenoxy)acetimidate

4-carboxybenzaldehyde-O-(2-carboxyphenoxy)oxime

4-carboxybenzaldehyde-O-(2-carboxyphenoxy)oxime

Conditions
ConditionsYield
With perchloric acid In 1,4-dioxane at 20℃;100%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

succinimidyl 4-formylbenzoate
60444-78-2

succinimidyl 4-formylbenzoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 25℃; for 14h;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;95%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;95%
tert-butyl diethylphosphonoacetate
27784-76-5

tert-butyl diethylphosphonoacetate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

(E)-4-(2-tert-Butoxycarbonylvinyl)benzoic acid
213462-15-8

(E)-4-(2-tert-Butoxycarbonylvinyl)benzoic acid

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane at 0 - 20℃; for 4h;100%
trimethyl phosphonoacetate

trimethyl phosphonoacetate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

methyl (E)-4-carboxyl cinnamate
115974-97-5

methyl (E)-4-carboxyl cinnamate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate; 4-Carboxybenzaldehyde With potassium carbonate In water at 0 - 20℃; for 1.5h;
Stage #2: In water pH=1; Acidic aqueous solution;
100%
With potassium carbonate In water at 0 - 20℃; pH=Ca. 2;95%
4-chloro-aniline
106-47-8

4-chloro-aniline

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-[(4-chlorophenylamino)methyl]benzoic acid
643012-91-3

4-[(4-chlorophenylamino)methyl]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-chloro-aniline; 4-Carboxybenzaldehyde In methanol for 0.5h; Heating / reflux;
Stage #2: With sodium cyanoborohydride; acetic acid In methanol at 20 - 35℃; for 0.5h;
Stage #3: With water In methanol at 20℃; for 16h;
100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

Conditions
ConditionsYield
In methanol100%
In dichloromethane
In dichloromethane
Multi-step reaction with 2 steps
1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
2: copper(II) bis(trifluoromethanesulfonate) / 16 h / 20 °C
View Scheme
methyl {4-(6-chloro-3'-ethyl-2-biphenylyl)-4-hydroxy-4-[(3R)-3-piperidinyl]butyl}carbamate
1070871-21-4

methyl {4-(6-chloro-3'-ethyl-2-biphenylyl)-4-hydroxy-4-[(3R)-3-piperidinyl]butyl}carbamate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

methyl (4-(6-chloro-3'-ethyl-2-biphenylyl)-4-{(3R)-1-[(4-formylphenyl)carbonyl]-3-piperidinyl}-4-hydroxybutyl)carbamate
1070870-93-7

methyl (4-(6-chloro-3'-ethyl-2-biphenylyl)-4-{(3R)-1-[(4-formylphenyl)carbonyl]-3-piperidinyl}-4-hydroxybutyl)carbamate

Conditions
ConditionsYield
Stage #1: 4-Carboxybenzaldehyde With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.166667h;
Stage #2: methyl {4-(6-chloro-3'-ethyl-2-biphenylyl)-4-hydroxy-4-[(3R)-3-piperidinyl]butyl}carbamate In dichloromethane for 0.583333h;
100%
6-(tert-butyl)-4-hydrazinothieno[2,3-d]pyrimidine
439692-56-5

6-(tert-butyl)-4-hydrazinothieno[2,3-d]pyrimidine

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-{[(6-tert-butylthieno[2,3-d]pyrimidin-4-yl)hydrazono]methyl}benzoic acid
439690-34-3

4-{[(6-tert-butylthieno[2,3-d]pyrimidin-4-yl)hydrazono]methyl}benzoic acid

Conditions
ConditionsYield
In benzene for 3h; Reflux;100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

methylamine
74-89-5

methylamine

4-[(Z)-Methyliminomethyl]-benzoic acid
35003-57-7

4-[(Z)-Methyliminomethyl]-benzoic acid

Conditions
ConditionsYield
at 20℃; for 12h;100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

t-butyl 3-N-t-butylaminopropionate
118264-59-8

t-butyl 3-N-t-butylaminopropionate

tert-butyl 3-(N-tert-butyl-4-formylbenzamido)propanoate
1393125-45-5

tert-butyl 3-(N-tert-butyl-4-formylbenzamido)propanoate

Conditions
ConditionsYield
Stage #1: 4-Carboxybenzaldehyde With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 5.5h; Reflux;
Stage #2: t-butyl 3-N-t-butylaminopropionate With triethylamine In dichloromethane at 20℃;
100%
3-Methyl-2-thioxo-thiazolidin-4-on
4807-55-0

3-Methyl-2-thioxo-thiazolidin-4-on

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-[(3-methyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid
1474053-19-4

4-[(3-methyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 180℃; for 0.0833333h; Knoevenagel Condensation; Microwave irradiation;100%
3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one
3889-20-1

3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-[(4-oxo-3-phenethyl-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid
1474053-30-9

4-[(4-oxo-3-phenethyl-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 180℃; for 0.0833333h; Knoevenagel Condensation; Microwave irradiation;100%
3-(4-methylbenzyl)-2-thioxothiazolidin-4-one
34392-97-7

3-(4-methylbenzyl)-2-thioxothiazolidin-4-one

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-[(3-(4-methylbenzyl)-4-oxo-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid
1474053-32-1

4-[(3-(4-methylbenzyl)-4-oxo-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 180℃; for 0.0833333h; Knoevenagel Condensation; Microwave irradiation;100%
1-(4-fluorophenyl)-2-(2-oxo-1,2-dihydropyridin-4-yl)ethane-1,2-dione
1620085-50-8

1-(4-fluorophenyl)-2-(2-oxo-1,2-dihydropyridin-4-yl)ethane-1,2-dione

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-(4-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoic acid
1620085-57-5

4-(4-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoic acid

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 180℃; for 0.166667h;100%
2-chloro-4-fluorobenzylamine
15205-11-5

2-chloro-4-fluorobenzylamine

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

N-[(2-chloro-4-fluorophenyl)methyl]-4-formylbenzamide

N-[(2-chloro-4-fluorophenyl)methyl]-4-formylbenzamide

Conditions
ConditionsYield
Stage #1: 4-Carboxybenzaldehyde With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide
Stage #2: 2-chloro-4-fluorobenzylamine In N,N-dimethyl-formamide at 20℃;
100%
β-alanine tert-butyl ester hydrochloride

β-alanine tert-butyl ester hydrochloride

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

tert-butyl 3-(4-formylbenzamido)propanoate

tert-butyl 3-(4-formylbenzamido)propanoate

Conditions
ConditionsYield
Stage #1: 4-Carboxybenzaldehyde With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.666667h;
Stage #2: β-alanine tert-butyl ester hydrochloride In N,N-dimethyl-formamide at 20℃; for 18h;
100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

N,N`-dimethylethylenediamine
110-70-3

N,N`-dimethylethylenediamine

4-(1,3-dimethylimidazolidin-2-yl)benzoic acid

4-(1,3-dimethylimidazolidin-2-yl)benzoic acid

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0333333h;100%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

2,7-bis-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl)-benzo-[lmn]-[3,8]phenanthroline-1,3,6,8-tetraone
261374-62-3

2,7-bis-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethyl)-benzo-[lmn]-[3,8]phenanthroline-1,3,6,8-tetraone

2,7-bis(2-(2-(2-(2-(4-formylphenylcarboxy)ethoxy)ethoxy)ethoxy)ethyl)benzo[lmn]-(3,8)phenanthroline-1,3,6,8-tetraone
1052073-35-4

2,7-bis(2-(2-(2-(2-(4-formylphenylcarboxy)ethoxy)ethoxy)ethoxy)ethyl)benzo[lmn]-(3,8)phenanthroline-1,3,6,8-tetraone

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 168h; Inert atmosphere; Darkness;99.5%
ethanol
64-17-5

ethanol

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

p-ethoxycarbonylbenzaldehyde
6287-86-1

p-ethoxycarbonylbenzaldehyde

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h;99%
With graphene oxide at 100℃; for 24h;90%
With sulfuric acid for 18h; Heating / reflux;83.1%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

malononitrile
109-77-3

malononitrile

(4-carboxybenzylidene)malononitrile
15725-53-8

(4-carboxybenzylidene)malononitrile

Conditions
ConditionsYield
With activated microporous polyurethane material with BET surface area of 312 m2 g-1 In tetrahydrofuran at 50℃; for 14h; Catalytic behavior; Knoevenagel Condensation;99%
With MIL-53(Fe) metal organic framework encapsulated on silica-coated nickel ferrite magnetic nanoparticles In ethanol at 20℃; for 1.16667h; Knoevenagel Condensation;97%
With (propyleneimine) dendrimer-G3 on silica coated magnetite nanohybrid In ethanol at 20℃; for 0.5h; Solvent; Knoevenagel Condensation; Inert atmosphere;95%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

3-hydroxymethyl-benzoic acid
3006-96-0

3-hydroxymethyl-benzoic acid

Conditions
ConditionsYield
With C55H44O2P4Ru; hydrogen at 80℃; under 38002.6 Torr; for 18h; Glovebox; Autoclave;99%
With C55H44O2P4Ru; hydrogen In tetrahydrofuran at 80℃; under 38002.6 Torr; for 18h; Inert atmosphere; Glovebox; Autoclave;99%
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran at 20℃; for 0.15h;96%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With hydrogen In ethanol at 100℃; under 2250.23 Torr; for 3h; Catalytic behavior; Inert atmosphere;99%
With W-7 Raney-Nickel In ethanol for 5h; Heating;89%

619-66-9Relevant articles and documents

-

Freidlin et al.

, (1972)

-

A Synergistic Magnetically Retrievable Inorganic-Organic Hybrid Metal Oxide Catalyst for Scalable Selective Oxidation of Alcohols to Aldehydes and Ketones

Mittal, Rupali,Awasthi, Satish Kumar

, p. 4799 - 4813 (2021/09/30)

Herein, we report a synergistic silica coated magnetic Fe3O4 catalyst functionalized with nitrogen rich organic moieties and immobilized with cobalt metal ion (FNP-5) for selective oxidation of alcohols to aldehydes and ketones using tert-butyl hydroperoxide (TBHP) as oxidant. The catalyst was rigorously characterized via several techniques which delineate its core-shell structure, magnetic behavior, phase and crystal structure. The Co(III) acts as the active catalytic center for selective oxidation reaction. The control reactions revealed radical mechanistic pathway assisted by the synergism induced by the inorganic-organic hybrid nature of FNP-5. The other features of current protocol involve neat reaction conditions, high TOF values, scalability of product and low E-factor value (1.92). Moreover, FNP-5 could be effortlessly separated via an external magnet, displays recyclability over eight catalytic cycles and exhibits structural integrity even after rigorous use. Overall, these results manifest the understanding of synergistic architectures as sustainable surrogates for selective oxidation reactions.

Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst

Mittal, Rupali,Kumar, Amit,Awasthi, Satish Kumar

, p. 11166 - 11176 (2021/03/31)

Herein, catalytic application of a metal-free sulfonic acid functionalized reduced graphene oxide (SA-rGO) material is reported for the synthesis of both carboxylic acids and their bioisosteres, 5-substituted-1H-tetrazoles. SA-rGO as a catalytic material incorporates the intriguing properties of graphene oxide material with additional benefits of highly acidic sites due to sulfonic acid groups. The oxidation of aldehydes to carboxylic acids could be efficiently achieved using H2O2as a green oxidant with high TOF values (9.06-9.89 h?1). The 5-substituted-1H-tetrazoles could also be effectively synthesized with high TOF values (12.08-16.96 h?1). The synthesis of 5-substituted-1H-tetrazoles was corroborated by single crystal X-ray analysis and computational calculations of the proposed reaction mechanism which correlated well with experimental findings. Both of the reactions could be performed efficiently at gram scale (10 g) using the SA-rGO catalyst. SA-rGO displays eminent reusability up to eight runs without significant decrease in its productivity. Thus, these features make SA-rGO riveting from an industrial perspective.

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes

You, Shengyong,Zhang, Rongli,Cai, Mingzhong

, p. 1962 - 1970 (2021/01/25)

A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.

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